کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1346846 1500336 2015 8 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Asymmetric Michael additions of a β-oxophosphonate to nitroalkenes in the presence of chiral diamine complexes
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی معدنی
پیش نمایش صفحه اول مقاله
Asymmetric Michael additions of a β-oxophosphonate to nitroalkenes in the presence of chiral diamine complexes
چکیده انگلیسی

Transition metal catalyzed asymmetric Michael additions of dimethyl (2-oxo-2-phenylethyl)phosphonate to a variety of aromatic nitroalkenes have been developed. The effects of ligand structure, metal ions, and solvent on the reaction are described. Ni(II)–bis[(1R,2R)-N,N′-dibenzylcyclohexane-1,2-diamine]Br2 was found to be an effective catalyst for this reaction. The corresponding adducts were obtained in the presence of this complex in good yields and with excellent enantioselectivity (up to 99% ee). The absolute configurations of the reaction products were determined by X-ray diffraction.

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Dimethyl [(2R,3S)-4-nitro-1-oxo-1,3-diphenylbut-2-yl]phosphonateC18H20NO6P[α]D20 = −38.4 (с 1.0, CHCl3)Absolute configuration: (2R,3S)Source of chirality: asymmetric catalysis

Dimethyl [(2R,3S)-3-(4-chlorophenyl)-4-nitro-1-oxo-1-phenylbut-2-yl]phosphonateC18H19ClNO6P[α]D20 = −34.7 (с 2.5, CH2Cl2)Absolute configuration: (2R,3S)Source of chirality: asymmetric catalysis

Dimethyl [(3S)-3-(2-chlorophenyl)-4-nitro-1-oxo-1-phenylbut-2-yl]phosphonateC18H19ClNO6P[α]D20 = −47.3 (с 2.5, CHCl3)Absolute configuration: (3S)Source of chirality: asymmetric catalysis

Dimethyl [(2R,3S)-3-(2-methoxyphenyl)-4-nitro-1-oxo-1-phenylbut-2-yl]phosphonateC19H22NO7P[α]D20 = −44.7 (с 2.5, CHCl3)Absolute configuration: (2R,3S)Source of chirality: asymmetric catalysis

Dimethyl [(2S,3R)-3-(3-methoxyphenyl)-4-nitro-1-oxo-1-phenylbut-2-yl]phosphonateC19H22NO7P[α]D20 = +42.4 (с 2.5, CH2Cl2)Absolute configuration: (2S,3R)Source of chirality: asymmetric catalysis

Dimethyl [(2R,3S)-3-(4-methoxyphenyl)-4-nitro-1-oxo-1-phenylbut-2-yl]phosphonateC19H22NO7P[α]D20 = −42.4 (с 2.5, CH2Cl2)Absolute configuration: (2R,3S)Source of chirality: asymmetric catalysis

Dimethyl [(2R,3S)-3-(3,4,5-trimethoxyphenyl)-4-nitro-1-oxo-1-phenylbut-2-yl]phosphonateC21H26NO9P[α]D20 = −35.6 (с 2.5, CHCl3)Absolute configuration: (2R,3S)Source of chirality: asymmetric catalysis

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron: Asymmetry - Volume 26, Issues 18–19, 15 October 2015, Pages 1050–1057
نویسندگان
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